| 1. Round | 10/08/2019 | FC Ingolstadt 04 [Youth] | - | Kickers Offenbach [Youth] | 0:1 | ||||
| 2. Round | 17/08/2019 | Kickers Offenbach [Youth] | - | VfB Stuttgart [Youth] | 1:2 | ||||
| 4. Round | 24/08/2019 | Karlsruher SC [Youth] | - | Kickers Offenbach [Youth] | 1:2 |  |
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| 5. Round | 15/09/2019 | Kickers Offenbach [Youth] | - | FC Augsburg [Youth] | 2:2 | ||||
| 6. Round | 22/09/2019 | 1. FC Kaiserslautern [Youth] | - | Kickers Offenbach [Youth] | 2:0 | ||||
| 3. Round | 25/09/2019 | Kickers Offenbach [Youth] | - | Eintracht Frankfurt [Youth] | 2:6 | ||||
| 7. Round | 29/09/2019 | Kickers Offenbach [Youth] | - | 1. FSV Mainz 05 [Youth] | 1:1 | ||||
| 15. Round | 01/02/2020 | VfB Stuttgart [Youth] | - | Kickers Offenbach [Youth] | 2:0 | ||||
| 16. Round | 07/02/2020 | Eintracht Frankfurt [Youth] | - | Kickers Offenbach [Youth] | 3:2 |
Germany
Portugal